110339-34-9

Usage

Uses

Used in Chemical Research:
2-(DiMethoxyMethyl)-5-(MethoxyMethyl)furan is used as a research compound for studying the reaction pathways of glucose during esterifications. Its unique structure allows for the investigation of glucose esterification mechanisms and the development of new synthetic methods and applications in the field of organic chemistry.
Used in Pharmaceutical Industry:
2-(DiMethoxyMethyl)-5-(MethoxyMethyl)furan can be used as a building block or intermediate in the synthesis of pharmaceutical compounds. Its specific functional groups and reactivity make it a valuable component in the development of new drugs and therapeutic agents.
Used in Flavor and Fragrance Industry:
Due to its unique chemical structure, 2-(DiMethoxyMethyl)-5-(MethoxyMethyl)furan may also be used as a component in the creation of novel fragrances and flavors. Its potential to impart distinct scents and tastes can be utilized in the development of new products in the flavor and fragrance market.

Upstream product

• 67-56-1 methanol 
• 67-47-0 5-hydroxymethyl-2-furfuraldehyde 
• 492-62-6 alpha-D-glucopyranose 
• 470-23-5 D-fructose 
• 10489-79-9 α-D-fructofuranose 
• 1917-64-2 5-(methoxymethyl)-2-furaldehyde 

Relevant academic research and scientific papers

Phosphotungstic acid heterogenized by assembly with pyridines for efficient catalytic conversion of fructose to methyl levulinate

Solid acid-catalyzed sugar degradation has been considered to be an efficient approach to synthesize alkyl levulinates (which can be used as fuel additives and surfactants). However, those catalytic processes typically involve harsh reaction conditions and high cost for catalyst preparation. We prepared a series of phosphotungstic acid organic hybrids by a simple solvothermal method, and used them as heterogeneous catalysts for the selective degradation of fructose to methyl levulinate (ML) in methanol with high efficiency under mild reaction conditions. The catalysts were characterized systematically, and the effects of different substituents in pyridine, reaction temperature/time, catalyst dose, and fructose concentration studied. The 3-FPYPW hybrid prepared from 3-fluoropyridine and phosphotungstic acid exhibited superior catalytic activity for the synthesis of ML (82.5%) from fructose (97.8%). A possible reaction pathway was proposed. In addition, the catalyst could be separated from the reaction mixture readily, and reused without remarkable loss of reactivity.

Etherification of 5-hydroxymethylfurfural using a heteropolyacid supported on a silica matrix

In this work, Preyssler-type heteropolyacids and their silica-included counterparts were employed in the etherification reaction of HMF and n-BuOH. Materials were synthesized with a Preyssler acid load of 12.5percent w/w using the sol-gel technique, which improved surface areas and modulated their acid strength. Prepared materials were used as heterogeneous solid acid catalysts in the selective etherification of 5-hydroxymethylfurfural (HMF) to 5-butoxymethylfurfural (5BMF). The high catalytic performance of the bulk Preyssler acids is related to their high acid strength, while selectivity related to the decrease in acidity by the inclusion effects. Different reaction parameters were optimized, with PWMo(12.5percent)&at;SiO2 exhibited the highest catalytic activity with 89percent of HMF conversion and 73percent of 5BMF selectivity. The catalyst is reusable up to five cycles without noticeable decrease in selectivity.

An efficient approach to synthesizing 2,5-bis(: N -methyl-aminomethyl)furan from 5-hydroxymethylfurfural via 2,5-bis(N -methyl-iminomethyl)furan using a two-step reaction in one pot

In this study, an amination-oxidation-amination-reduction (AOAR) strategy was proposed for the synthesis of 2,5-bis(N-methyl-aminomethyl)furan (BMAF) from HMF via the intermediate 2,5-bis(N-methyl-iminomethyl)furan (BMIF). Firstly, an efficient synthesis of BMIF from HMF using a one-pot amination-oxidation-amination reaction was developed over α-MnO2 under an air atmosphere. A BMIF yield of 98.3% was obtained under mild reaction conditions. The conversion of HMF to BMIF underwent the fast amination of HMF to 5-(methyl-iminomethyl)furfuryl alcohol (MIFA), the subsequent rate-limiting oxidation of MIFA to 5-(methyl-iminomethyl)furfural (MIFF) and the final fast amination of MIFF to BMIF. The quick amination of MIFF to BMIF drove the oxidation reaction equilibrium toward MIFF from MIFA, which ensured the highly efficient conversion of HMF to BMIF. The investigation of the catalytic mechanism showed better lattice oxygen donating ability and oxygen coordination capacity, which made α-MnO2 retain the structural stability in the reaction. The higher ratio and better mobility of the lattice oxygen endowed α-MnO2 with excellent catalytic performance in the oxidation of MIFA to MIFF by the redox cycling of Mn4+/Mn3+, facilitating the conversion of HMF to BMIF. Eventually, a BMAF yield of 96.1% was achieved by the reduction of BMIF with Ru/C after the AOA reaction, realizing the synthesis of BMAF from HMF using a two-step reaction in one pot. This journal is

Etherification of biomass-derived furanyl alcohols with aliphatic alcohols over silica-supported nickel phosphide catalysts: Effect of surplus P species on the acidity

The acidity of nickel phosphide (Ni2P) catalysts plays a crucial role in producing a desired hydrodeoxygenation molecule from biomass-derived substrates; yet, it has never been explored in acid-catalyzed reactions. Herein, we demonstrated the activity of silica-supported Ni2P catalyst prepared with the nominal P/Ni ratio of 2 (Ni2P/SiO2-2P) in the etherification of furanyl alcohols (particularly, 5-(hydroxymethyl)furfural) with aliphatic alcohols including ethanol. By comparing the characteristics of Ni/SiO2, PxOy/SiO2, and Ni2P/SiO2-xP (x = 0.5 and 1), Ni2P/SiO2-2P was revealed to contain the Br?nsted and Lewis acid sites of which both contributed to the etherification reaction. Notably, the Br?nsted acidity was associated with the surplus P species added to produce the Ni2P phase. Consequently, supported Ni2P catalysts can work in acid-catalyzed reactions if an adequate ratio of Br?nsted to Lewis acid sites is provided by the amount of the surplus P species determined by adjusting the P/Ni ratio.

A bifunctional cerium phosphate catalyst for chemoselective acetalization

Acid-base solid catalysts synthesized with structurally controlled uniform active sites can lead to unique catalysis. In this study, a CePO4 catalyst was synthesized using a hydrothermal method and found to exhibit high catalytic performance for the chemoselective acetalization of 5-hydroxymethylfurfural with alcohols, in sharp contrast to other homogeneous and heterogeneous acid and/or base catalysts. In the presence of CePO4, various combinations of carbonyl compounds and alcohols are efficiently converted into the corresponding acetal derivatives in good to excellent yields. Mechanistic studies show that CePO4 most likely acts as a bifunctional catalyst through the interaction of uniform Lewis acid and weak base sites with 5-hydroxymethylfurfural and alcohol molecules, respectively, which results in high catalytic performance.

METHOD OF PRODUCING 5-HYDROXYMETHYLFURFURAL FROM CARBOHYDRATES

Disclosed herein is a process for preparing 5-hydroxymethylfurfural comprising the step of contacting a carbohydrate and a Br?nsted acid in an alcoholic solvent comprising an alcohol selected from the group consisting of secondary alcohols, tertiary alcohols, aryl alcohols and combinations thereof under conditions to dehydrate the carbohydrate thereby forming a reaction product containing 5-hydroxymethylfurfural.

The production of 5-hydroxymethylfurfural from fructose in isopropyl alcohol: A green and efficient system

Solving problems: An isopropyl alcohol-mediated reaction system for the production of 5-hydroxymethylfurfural (HMF) from fructose reaches a yield of up to 87 %. The solvent can be easily recycled by evaporation, giving the HMF product. The system avoids the use of large amounts of organic solvent, has a minimal environmental impact, and offers a new route to large-scale economically viable processes.

Levulinic esters from the acid-catalysed reactions of sugars and alcohols as part of a bio-refinery

Polymeric humin formation greatly diminishes levulinic acid yields in acid treatment of C6 sugars in aqueous medium. Protecting reactive functional groups of sugars and reaction intermediates via acetalisation and etherification in methanol medium effectively suppresses humin formation and remarkably enhances the production of levulinic esters.

Photo-oxygenation des derives de l'hydroxymethyl-5 furfural-2

Photosensitized oxygenations in alcoholic solution of the furfural compounds 1,6-9 and the furanic compounds 10-17 yield the hydroxybutenolides 2a, 1, 20, 21, 22, the alkoxybutenolides 5, 19, 23, 24 and the unsaturated compounds 25 and 26.With rose bengal fixed on the polysaccharide resin Sephadex A 25 as sensitizer, the quantum yields of singlet oxygen formation in methanol or ethanol are higher (19 to 116percent) than those obtained with the commercial resin Sensitox.Kinetic results for these photo-oxygenations show the electronic influence of the substitution on C2 or C5.Depending on these substituants, several reaction pathways can be envisaged in order to explain the formation of the products.